Powerful Women Share Their Thoughts on Leadership

Being a true leader isn’t about securing a fancy title or a having certain number of people working for you. After all, most of us have probably had managers who, despite an impressive career path and prestigious status, utterly failed to inspire. So, then, what exactly does it take to become the kind of magnetic luminary who can motivate others to get behind you and rev up excitement for your cause? And how do you know if you’ve got it?

We asked six women at the top of their game to describe the crystallizing moment when they realized they were leaders.

When I Had to Make a Large Presentation at the Last Minute

Who: Robin Koval is an award-winning marketing and advertising expert and best-selling author. She leads Legacy, the nation’s largest public health foundation devoted to tobacco use prevention and cessation.

As co-founder of the Kaplan Thaler Group advertising agency, Koval grew it from a startup to a billion-dollar company, ultimately serving as CEO of Publicis Kaplan Thaler, New York’s fifth-largest ad agency. Koval and her business partner have written three books; their latest, Grit to Great: How Perseverance and Pluck Can Take You from Ordinary to Extraordinary, will be published in September.

The moment: “A few weeks before my 30th birthday, I had been burning the candle at both ends preparing for the most important meeting of the year with one of our largest clients. My job as an account manager at a top New York advertising agency was to make my boss look great. He was giving the lion’s share of the presentation I had slaved over.

“The morning of the meeting, we all met at the airport. The president of my agency and the chief creative officer were there. But my boss wasn’t. He had become ill the night before and couldn’t make the trip. The president looked at me and said, ‘I guess that means you’re up. You have a 90-minute plane ride to learn his part.’

“I was rattled but determined. Although I wasn’t born with virtuoso talent or an Ivy League legacy, growing up in the Bronx had given me a lot of homegrown grit. I drew on a combination of guts, resilience, initiative, and tenacity as I furiously prepared on that way-too-short flight.

“I made the presentation and it went over with flying colors. The president of the agency leaned over and whispered: ‘Wow, Robin, you really showed me what you’re made of today. I’m blown away.’ I knew in my head, heart, and gut that I had made the transition to leadership that day. Not too long afterward, I became the youngest-ever woman [executive VP] at my agency.”

When I Saw a Young Attorney I Mentored in Court

Who: Rebecca LeGrand, 39, has been practicing law for 10 years. Since 2012, she has helped lead the law firm Kaiser, LeGrand & Dillon, which represents people and businesses in civil litigation, government investigations, and white-collar criminal cases. She was also recognized by Super Lawyers as a “Rising Star” in litigation.

LeGrand has a J.D. from Yale Law School, but she also earned a master’s in evolutionary biology from Duke — before realizing her love for law, she was a self-proclaimed science nerd.

The moment: “I remember first really feeling like a leader two years ago, when I watched a young attorney I’d hired and mentored argue in court for the first time. I knew she was a very talented lawyer, but she had been incredibly nervous about speaking in court.

“We worked together to prepare for the argument, and when she stood up to make her case she did an amazing job. Her voice filled the courtroom, and she projected confidence and competence to everyone present. Helping to lead an organization that excels at training and mentoring young lawyers is something I’m incredibly proud of.”

When I Got Laid Off

Who: Chia-Lin Simmons is the head of global partner marketing for Google Play and is launching her own company, Looky Loo, a mobile social startup focused on fashion. She also served as the vice president of marketing at Harman International, general manager of Playphone, and vice president of strategic alliances at Audible.

Simmons is the co-host of On Digital Media, a podcast on technology and the monetization of digital media. She holds degrees from U.C. San Diego, George Mason University School of Law, and Cornell University, where she was a Park Leadership Fellow.

The moment: “I recognized I was a leader when I experienced my first layoff. At the time, I was 26 years old and a director of marketing, and our startup did not secure our series B funding. Although I was not an executive at the company, I felt responsible for the livelihood of the team.

“The minute after we heard the bad news, I started calling everyone I knew to help place my staff into new roles at other companies. I knew at that minute that leadership was not just about leading the team when times were good, but also not abandoning my team when things were going south.”

When I Freelanced and Ran My Own Outfit

Who: As the founding editor of espnW, Alison Overholt defined the product vision and editorial strategy for the company’s multi-platform expansion into sports media for women. She is also an adjunct professor at NYU’s Robert Preston Tisch Center, where she teaches applied research methods to students in the sports management, hospitality, and tourism departments.

The moment: “Leadership has always been in my DNA. I was never the best basketball player on the team in high school, but I was captain. I wasn’t the best singer or soloist in my college a cappella group, but I was tour manager and then president, organizing tours to southeast Asia and overseeing a pretty significant budget.

“In my career, I had a few management roles as an editor early on. But ironically, it was actually when I was freelance, running my own content strategy outfit, that I felt like a leader in that intrinsic way. I was a hired gun for a Web agency to help redesign The Breast Cancer Research Foundation’s website, and as we worked on the project it was clear that we weren’t just redoing a site, we were rethinking an organization’s identity, right down to the logo and mission statement. I very naturally took on a leadership role in those strategy sessions, both within the agency and with the client.

“The day we presented a two-hour deck of ideas to the board, including the legendary marketing executive Leonard Lauder, the team from the agency put me out in front to carry the presentation and lead the sessions that followed — and it felt exactly right. I felt like a leader in that moment and it had nothing to do with a formal title. That internal confidence is something I’ve carried with me since.”

When I Was Working on a Group Project

Who: Himalayan-born Tapasya Bali is the co-founder and chief operating officer of YogaSmoga, a designer, manufacturer, and retailer of yoga-inspired athletic apparel and accessories. She was also instrumental in forming the Namaskar Foundation, a nonprofit that supports health, education, and microlending efforts in developing countries. Bali holds an MBA from New York University and was a senior director at Credit Suisse before launching her company.

The moment: “A few years into my first career on Wall Street, my group was working on an important, time-sensitive project. I found coworkers gravitating toward me for direction at every step, and I soon realized that I was starting to form a trust among people, where they were not only following my direction but were also looking to me for motivation and validation to get over the hump and deliver the project on time. It struck me then that I was a leader.”

When I Compared Myself to My Mom

Who: Catherine Merritt has worn many hats throughout her career, from running a district office for an Illinois state senator to hawking steaks as the head of global PR for Morton’s Restaurant Group. Currently, she is vice president at the PR firm Olson Engage, specializing in brands that attract and market to moms. She is also the founder of Mumzy, a crowdfunding site for moms.

The moment: “My mom has always been my role model in many ways, but especially in how she grew a thriving career while raising our family. Not long ago, I had a profound moment: I was leading two huge accounts within my day job at a marketing agency, was launching a new startup, and twice in one week I’d been able to be snack helper at my sons’ preschool, when it hit me that not only am I a leader within my roles throughout my career, but I’m also a leader within my family — as well as a loving mother. When I compared myself to my mom at that moment, the woman I’ve been striving to be, that’s when I first felt like a true leader.”